HCID 178418361, compound → HCID 178510722, compound

HRID 1577561Notes

Reaction equation

HRID 1577561 reaction equation
[NH2:1]/[C:2](/[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-])=O)=[C:3]1\[C:4](=[O:12])[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[S:7]\1.[H][H]>C(OC)(=O)C.O1CCCC1.[Ni]>[NH2:1]/[C:2](/[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH2:19])=[C:3]1\[C:4](=[O:12])[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[S:7]\1

Participants

6

Reactant 2

HCID 178418361HCID 178418361, compound2×HCID 178510724HCID 178510724, compound

Product 1

HCID 178510722HCID 178510722, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 6584Methyl AcetateSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.5 gm (0.00168 mol) of (E)-2-[(amino)-(2-nitrophenyl)methylene]-benzo[b]thiophen-3(2H)-one was dissolved in a mixture of 10 cc of methyl acetate and 10 cc of tetrahydrofuran, and after adding 0.5 gm of Raney nickel the mixture was hydrogenated at room temperature and a hydrogen pressure of 5 bar until hydrogen uptake was at an end. The catalyst was then filtered off, the solvent was evaporated at reduced pressure, and the residue was recrystallized twice in the presence of activated charcoal from tetrahydrofuran/petroleum ether (1:1). 330 mgm (73% of theory) of yellow crystals were obtained, m.p. 186°-187° C. (petroleum ether/tetrahydrofuran 1:1).

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe catalyst was then filtered off
  3. customthe solvent was evaporated at reduced pressure
  4. customthe residue was recrystallized twice in the presence of activated charcoal from tetrahydrofuran/petroleum ether (1:1)
  5. custom330 mgm (73% of theory) of yellow crystals were obtained

Sources & evidence

ORD record
ord-fcd180e911c84e1990b29480e27219e7
Source dataset
uspto-grants-1981_09
Patent number
US04288437

Reaction notes

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